"Summer, Kind of Wonderful" is the 19th episode of the CW television series, Gossip Girl, as well as the season premiere of the show's second season. The episode was written by Joshua Safran and directed by J. Miller Tobin. It originally aired on Monday, September 1, 2008 on the CW. "Summer, Kind of Wonderful" premieres in the Hamptons with the summer nearly drawing to a close. Serena van der Woodsen (Blake Lively) spends the summer attempting to move on from her previous relationship with Dan Humphrey (Penn Badgley), who himself also has trouble moving on to the point that it has affected his internship with a famous author. Chuck Bass (Ed Westwick) awaits the arrival of Blair Waldorf (Leighton Meester) from her European trip but finds her already in a new relationship with James Schuller (Patrick Heusinger) who is hiding his own secrets from Blair. Nate Archibald (Chace Crawford) uses his fake relationship with Serena to conceal his affair with an older, married woman named Catherine Mason (Mädchen Amick) while Jenny Humphrey (Taylor Momsen) finds herself interning at Eleanor Waldorf Designs, subsequently reconciling with Eric van der Woodsen (Connor Paolo) to impress her boss. Plot The episode reveals Blair, Serena, Nate and Chuck spending their summer in the Hamptons and opens with Nate having an affair with a woman named Catherine while he and Serena mislead people into thinking that they are together. During one their trysts, Catherine's husband returns home early and she drives Nate out of the house. Barely clothed and running for the street, he runs into Serena and her date and Serena discovers Nate's affair. Nate soon develops feelings for Catherine and arrives with Serena as a date to the White party to make Catherine jealous. Serena helps Nate make her jealous by kissing him in public but is shocked to find a displeased Dan witnessing the entire scene. Serena's plan eventually works for Nate as Catherine becomes jealous and the two sleep with each other during the party. Chuck is seen spending his summer with other women and prepares to impress Blair by meeting her at the bus stop of the Hamptons jitney, fresh from her travels. Blair returns but is seen with a new man, James, whom Blair uses to make Chuck jealous. During lunch at their Hamptons house, Chuck's attempts to ruin Blair reveals Blair's conflicted feelings for Chuck but chooses not to